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Alcohols

Alcohols. Nomenclature Properties Preparation Reactions Spectroscopy. Alcohol Nomenclature. IUPAC Common Carbinol. Preparation Reactions. Reduction of carbonyl compounds Hydration of Alkenes Grignard reactions. Reduction of Carbonyl Compounds. Reduction of Aldehydes/ketones

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Alcohols

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  1. Alcohols • Nomenclature • Properties • Preparation • Reactions • Spectroscopy

  2. Alcohol Nomenclature IUPAC Common Carbinol

  3. Preparation Reactions • Reduction of carbonyl compounds • Hydration of Alkenes • Grignard reactions

  4. Reduction of Carbonyl Compounds • Reduction of Aldehydes/ketones • Reduction of Carboxylic acids/Esters

  5. Reduction of Aldehydes/Ketones Hydrogenation

  6. Reduction of Aldehydes/Ketones Hydride Reductions

  7. Reduction of Carboxylic Acids and Esters Lithium Aluminum Hydride Reduction

  8. Hydration of Alkenes • Acid catalyzed Hydration • Oxymercuration-Demercuration • Hydroboration-Oxidation

  9. Acid-Catalyzed Hydration of Alkenes • Markovnikov addition • Formation of most stable carbocation • Shifts/rearrangements possible

  10. Hydration of Alkenes via Oxymercuration/Demercuration • Markovnikov addition • Typically no shifts/rearrangements • Mercurinium ion involvement

  11. Hydroboration-Oxidation of Alkenes • Anti-Markovnikov addition • No shifts/rearrangements • Syn addition

  12. Grignard Addition Reactions • Addition to Aldehydes/Ketones • Addition to Esters • Addition to Epoxides

  13. Grignard Additions to Aldehydes/Ketones Formation of primary, secondary, and tertiary alcohols

  14. Grignard Additions to Esters Formation of secondary and tertiary alcohols

  15. Grignard Addition to Epoxides

  16. Salt formation Dehydration Oxidation Alkyl halide formation Ester formation Ether synthesis Periodic acid cleavage of glycols Haloform reaction of methyl carbinols THP acetal formation Typical Alcohol Reactions

  17. Conversion of Alcohols to Salts Reaction with Active Metals

  18. Dehydration of Alcohols

  19. Oxidation of Alcohols

  20. Alcohol Conversion to Alkyl Halides • Reaction with Hydrogen halides • Reaction with Thionyl chloride • Reaction with Phosphorus trihalides or pentahalides

  21. Hydrogen Halide Conversion of Alcohols to Alkyl Halides

  22. Conversion of Alcohols to Alkyl Chlorides via Thionyl Chloride

  23. Conversion of Alcohols to Alkyl Halides via Phosphorus Halides

  24. Ester Formation from Alcohols

  25. Periodic Acid Cleavage of Glycols

  26. Haloform Reaction Methyl carbinol cleavage to give Carboxylic acids and Haloform

  27. Disguising an Alcohol Creating a tetrahydropyranyl acetal

  28. Spectroscopic Characteristics of Alcohols • Infrared • Pmr • Cmr

  29. Ethers • Nomenclature • Properties • Preparation • Reactions

  30. Ether Nomenclature

  31. Preparation of Ethers Dehydration of Alcohols Williamson synthesis Alkoxymercuration- Demercuration Peroxyacid Epoxidation of Alkenes

  32. Ether Formation via Acid Catalyzed Dehydration of Alcohols

  33. Williamson Synthesis of Ethers Bimolecular Substitution by Alkoxide on a suitable substrate

  34. Alkoxymercuration-Demercuration of Alkenes • Markovnikov Addition • Typically no rearrangements/shifts • Mercurinium ion involvement

  35. Epoxidation of Alkenes Prilezhaev reaction

  36. Ether Reactions • HX Cleavage • Epoxide Ring Opening

  37. HX Cleavage of Ethers Unimolecular or Bimolecular Cleavage Pathways

  38. Epoxide Ring Opening Unimolecular or Bimolecular

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